Myrcenol

Myrcenol is an organic compound, specifically a terpenoid. It is most notable as one of the fragrant components of lavender oil.

Myrcenol
Names
Preferred IUPAC name
2-Methyl-6-methylideneoct-7-en-2-ol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.040
UNII
  • InChI=1S/C10H18O/c1-5-9(2)7-6-8-10(3,4)11/h5,11H,1-2,6-8H2,3-4H3 ☒N
    Key: DUNCVNHORHNONW-UHFFFAOYSA-N ☒N
  • InChI=1/C10H18O/c1-5-9(2)7-6-8-10(3,4)11/h5,11H,1-2,6-8H2,3-4H3
    Key: DUNCVNHORHNONW-UHFFFAOYAC
  • C=CC(=C)CCCC(C)(C)O
Properties
C10H18O
Molar mass 154.24 g/mol
Density 0.85 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

It is also found in the hop plant (Humulus lupulus). E-Myrcenol acts also as a pheromone for bark beetles.[1]

Role in fragrance industry

Myrcenol is obtained synthetically from myrcene via hydroamination of the 1,3-diene followed by hydrolysis and Pd-catalysed removal of the amine. As a 1,3-diene, myrcenol undergoes Diels-Alder reactions with several dienophiles such as acrolein to give cyclohexene derivatives that are also useful fragrances.[2]

References
  1. E-Myrcenol in Ips duplicatus: An aggregation pheromone component new for bark beetles. Byers, J.A., Schlyter, F., Birgersson, G., & Francke, W. 1990 Experientia 46:1209-1211.
  2. Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a11_141
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